1-Phenyl-3-methyl-4-penten-1-yne | 34600-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Phenyl-3-methyl-4-penten-1-yne
• 英文别名: 2-vinyl-4-phenyl-3-butyne；3-Methylpent-4-en-1-ynylbenzene
• CAS: 34600-24-3
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: OUUFFFBTCQBIIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  231.6±19.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 1-Phenyl-3-methyl-4-penten-1-yne 生成 Trimethyl-(3-methyl-1-phenyl-penta-1,2,4-trienyl)-silane
  参考文献：
  名称：

  Klein,J. et al., Israel Journal of Chemistry, 1971, vol. 9, p. 177 - 184

  摘要：

  DOI：
• 作为产物：
  描述：

  copper(I) phenylacetylenide 、 1-氯-2-丁烯 在 盐酸 作用下， 生成 1-Phenyl-3-methyl-4-penten-1-yne
  参考文献：
  名称：

  Copper(I) substitutions. Scope and mechanism of cuprous acetylide substitutions

  摘要：

  DOI：

  10.1021/ja01051a049

文献信息

• Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases
  作者：Lothar W. Bieber、Margarete F. da Silva

  DOI：10.1016/j.tetlet.2007.08.010

  日期：2007.10

  Allylic halides and terminal alkynes couple under CuI catalysis in DMSO or DMF solution. In most cases, sodium carbonate or bicarbonate is sufficient to promote the reaction; less reactive alkynes require catalytic amounts of DBU. Bifunctional alkynes and halides can be reacted selectively according to the stoichiometry used. Trimethylsilyl, hydroxyl, ester and halide groups are tolerated in the alkyne

  烯丙基卤化物和末端炔烃在CuI催化下在DMSO或DMF溶液中偶联。在大多数情况下，碳酸钠或碳酸氢钠足以促进反应。反应性较低的炔烃需要催化量的DBU。双官能炔烃和卤化物可以根据所用的化学计量选择性地反应。炔烃中可容忍三甲基甲硅烷基，羟基，酯和卤化物基团。大多数卤化物反应时不进行烯丙基重排。该方法适合于官能化的炔烃的合成。
• Synthesis of trifluoromethylated allenes via visible light-promoted bis(trifluoromethylation) of 1,3-enynes
  作者：Yu-Rou Zhao、Yanchen Zhou、Mingyou Hu

  DOI：10.1016/j.jfluchem.2023.110105

  日期：2023.4

  A visible light-promoted/copper-mediated 1,4-bis(trifluoromethylation) method of easily available 1,3-enynes to construct allenic Csp2−CF3 bonds has been described. The reaction proceeded under mild conditions, has broad substrate scope and good functional group tolerance. Photocatalyst is not required in this protocol, and O2 plays an important role in facilitating the trifluoromethyl group transfer

  已经描述了一种可见光促进/铜介导的 1,4-双（三氟甲基化）方法，该方法使用容易获得的 1,3-烯炔来构建联烯型 Csp 2 -CF 3键。反应条件温和，底物范围广，官能团耐受性好。该方案不需要光催化剂，O 2在促进三氟甲基转移​​和提高产率方面起着重要作用。机理研究表明，该反应涉及一个激进的过程。
• Nickel-catalyzed cross-coupling reaction of allyl halides with alkynyltins
  作者：Dong-Mei Cui、Naoko Hashimoto、Shin-ichi Ikeda、Yoshiro Sato

  DOI：10.1021/jo00123a006

  日期：1995.9

  A cross-coupling reaction of allyl halides 1 with alkynyltins 3 in the presence of ''Ni(PR(3))(n)'' (R = Ph, Oft, or OPh) catalyst was carried out in THF at reflux to give 1,4-enynes, The regioselectivity of the coupling of 1f-i with 3a was investigated in the presence of various phosphorus ligands. Interestingly, prenyl (1j) and geranyl chlorides (1k) selectively reacted with 3 at the more-hindered positions of substituted eta(3)-allylnickel intermediates 21 (M = Ni) to yield 23 and 25, respectively. Regioselectivity in these reactions may result from greater steric crowding between the phosphorus ligand and the disubstituted position in 26b than in 26a. In contrast, the palladium-catalyzed reactions of 1j and 1k with 3 selectively gave 22 and 24, respectively. Thus, the steric crowding in a Pd analogue of 26b is less than that in a Ni analogue of 26b, since Pd has a larger covalent radius than Ni.
• Matveeva; Erin; Kurz, Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1061 - 1064
  作者：Matveeva、Erin、Kurz

  DOI：——

  日期：——
• A new catalytic synthesis of non-conjugated alkenynes
  作者：M. Catellani、G.P. Chiusoli、G. Salerno、F. Dallatomasina

  DOI：10.1016/s0022-328x(00)88762-8

  日期：1978.2